
Villa vacation rentals in Montaione
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Top-rated villa rentals in Montaione
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Private villa rentals

Luxury Villa on Chianti Wine Estate
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.

Church of the Vaioni
The renovated church was incredibly interesting and I was fascinated by its long history. The church is nestled within a tranquil olive grove which made it easy to relax and disconnect from the stressors of the big city. Roberto was absolutely incredible and I cannot give higher praise—he is truly the standard when it comes to hosts. He was attentive, responsive to any issues, and helpful to solve any difficulties that we had with travel arrangements. It’s easy to see why this property is in such high demand. It was my first time staying in Tuscany and Roberto’s church is already calling me back for another stay! Most highly recommended.

Sestuccina
We had a lovely stay at this beautiful villa. The photos do not do it justice at all! From the infinity pool overlooking the vineyard to the hot tub with views of a castle, it was stunning and jaw dropping scenery. Brigittia made sure we were prepared to have a great trip - from helping us with reservations and arranging transportation for us with her husband (who was wonderful) she was a fantastic host. We would love to visit again sometime and would recommend for anyone wanting to spend time in the countryside.

Luxury Tuscany Villa on the hill with private pool
We booked this for a girls holiday and we had the best week. We didn’t hire a car, we walked to a few of neighbouring towns and got a taxi to Lucca, and a train to Florence one day. Neighbouring towns have small supermarkets and the walks to them were enjoyable, the scenery is truly incredible. Lucca is beautiful and has incredible markets, it’s a must see if you stay here. The villa itself is exactly as shown in the pictures, the pool area is gorgeous, we sat around the table every night for dinner, and when it’s dark there’s clusters of fireflies sparkling in the roses, it was magical. Stefania was great, very responsive and there if we needed her. We’d definitely recommend and book this villa again in the future!

The Lazy Oak
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!

Beautiful tuscan country house
The house is beautiful and very big. It is located just outside of Buonconvento and offers complete privacy. A car is an advantage. The rooms are spacious, there are mosquito nets above all beds and enough bathrooms and toilets for everyone. In general, the house is very well equipped, both in the kitchen and otherwise. The pool is slightly elevated, beautiful, large, with natural shade all around and offers a magnificent view on the surrounding countryside. In the huge garden you can eat, linger, play... There is even a small basketball court. But beware: right next door there are wild blackberries and the ball can be lost :) In Buonconvento there is a coop, a fine gelateria and a good coffee with the famous and fine products of Le Dolcezze di Nanni. For a good pizza, the drive to the Mulinum restaurant is worth it a little outside, they have their own mill and process their own grain. We highly recommend the house.

Villa sii felice
We had an unforgettable stay at this villa for our bachelorette getaway! The host was incredibly responsive and made everything smooth from start to finish. The views were absolutely breathtaking — even better than in the pictures! The villa had everything we needed to set the perfect atmosphere: fully stocked kitchen with plates and glasses, plenty of towels, and thoughtful details throughout. We loved picking fresh lemons from the garden and finding peaceful spots around the property to read and relax. It’s incredibly private and serene — the perfect escape. While the drive-up can be a bit tricky at first, it quickly becomes second nature and is well worth it.This place exceeded all of our expectations. Highly, highly recommend — we'd come back in a heartbeat!

Panoramic" Casa Gello" with private pool.
We've just arrived back in England after a lovely May half-term week at Monica's house - around 50 mins drive from Pisa airport. We are a family of four, so the kids shared the second bedroom and there was more than sufficient living space. The gardens are beautiful, pool clean and stylish and views amazing at the top of a hill. The air con was welcome as the weather hotted up and great selection of DVDs were very useful in the evenings. We were able to visit Florence, Siena and San Gimignano easily in our hire car. With local restaurants and supermarkets a short drive away, the house remained close enough to everything we needed yet far enough away from any town for it to give us the rest and peace we needed. Thank you Monica for sharing your home with us and the great recommendations and contact - we will definitely try to book again for any other trip to Tuscany.
Luxury villa rentals

Valluccia 51
We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.

Truly Tuscan villa with pool 6km to San Gimignano
As soon as you get out of the car we smelled jasmine. The grounds are so well attended to. Beautiful roses, rosemary bushes everywhere! The pool is much larger than the pictures appear. The views are incredible!! It was the perfect place for us and our adult children with significant others. Our daughters boyfriends family joined us from Great Britain and our other daughter got engaged during our vacation in the backyard of the villa at twighlight. We will never forget this place and the very many memories that it provided. The villa was so comfortable with all the amenities. We were cooking outside and relaxing by the pool daily. Giulia provided a special wine tasting recommendation day of arrival and we also enjoyed our favorite wine tasting right down the road at Corbucci. Do not miss this whatever you do!! Many wonderful days exploring Chianti country also Florence and Sienna close by. Thanks for the BEST holiday ❤️🍷❤️ thank you for making us so comfortable !!

Villa Le Panteraie - located between Florence and Pisa
A beautiful villa with exceptional views to the hills and valley. Various oudoor areas. Private location however close to sights and amenities. Cafes and restaurants not far however not walking distance, best accessed by own car. Electric bikes were available for sightseeing. Fantastic host, always responsive and helpful. Can warmly recommend.

Romantic Villa with private pool and fabulous view
Most beautiful villa with so much charm! Fantastic location as well, easy to explore Florence, Siena, San Gimignano, as well as all the surrounding wineries and countryside. The villa was so lovely that we decided to spend 2 days in the villa, chilling at the pool drinking wine and having tapas! Janine is a great host with many recommendations of what to do in the local area. Highly recommended to stay here to experience Tuscany!

Exclusive Farmhouse Pool & View of San Gimignano
This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!

Old renovated mill in the Tuscan hills
You can stop looking now! This is probably the most perfect place to stay and with the best host in all of Tuscany. This is said by a very travel and quite picky family from Sweden that this time went with three sons 16, 18 and 22 and the eldest son's fiancée. The host Lorenzo is absolutely amazing both before and during the stay: quick responses, incredibly helpful and very accommodating. You live in a renovated mill (two super-fresh separate buildings one of which is newly built) in the small village of Montefoscoli, with wonderful views of the landscape and sun location from morning till night. Large patio with barbecue and pool for lovely meals and relaxing. Inside there is everything you need and more: full equipped kitchen, dishwasher, washing machine, ironing equipment, ac in each bedroom. Good wifi and TV box. Excellent little bakery 50 meters from the residence. A small Coop shop 5 minutes walking distance from the residence with everything you need. We've already told friends and acquaintances about this home — it won't be better!

La Dolce Vita - Tuscan experience
We had a wonderful stay, the house really felt like a home and was instantly relaxing. The whole booking and check in process was very straightforward and Giuseppe who met us to show us around the property and hand over the keys was very welcoming, kind and informative. The house has wonderfully peaceful location, with beautiful views. It has been furnished with excellent taste, and so adds to the feeling of being in a real home rather than a rental. The gardens and pool are delightful and evenings on the loggia will be remembered for a long time, we cant wait to return!

Farmhouse , pool, 13 px. Lucca 10km
We had an amazing stay at Juri's beautiful villa in Tuscany! The place is super spacious, easily accommodating our group of 11, and it was spotless and very well maintained. Juri and his mom were incredible hosts—always responsive and ready to help whenever we needed anything. The location is also perfect for day trips to Florence, Pisa, and Lucca. If you're looking for a charming, well-kept and very clean villa with top-notch hospitality, this is the place. Highly recommend! Let me know if you'd like any tweaks!
Villa rentals with a pool

Dream in Tuscany, Villa with pool
Six of us spent a wonderful week at Vicky's villa to celebrate my husband's 60th birthday. The beautifully appointed house, the stunning views, and the swimming pool were all we had hoped for and more. Vicky is a five-star host. She welcomed us and even arranged to have a meal served upon our arrival. She generously helped us coordinate a catered birthday dinner at the villa. She shared interesting stories and lore from the area and made us feel very much at home. Before we left, she even took us on a tour of the magnificent Medici building under restoration on her property. From the villa, we headed out to Livorno, Pisa, Siena, and Florence, each a manageable day trip through the rolling Tuscan countryside. (Note: The final approach to the villa is over unpaved road; we were happy to have chosen an SUV for our rental.) We are left with great memories and many beautiful photographs of our stay in Peccioli. Thank you, Vicky!

Tuscan Dream Villa @ Rustic Elegance Near Florence
We enjoyed our stay at Il Casellino. The property is beautiful and peaceful. Super clean and very friendly host. Not a walkable location so driving a car is a must to come and go, nearest stores and restaurants are less than 10 minutes away but very worth it if you are looking for amazing panoramas. The pool area was better than the pictures!

Villa Belvedere beautiful view surrounded by greenery
Genka was the perfect host from start to finish, and the villa surpassed our expectations. Communication with Genka was great - he was quick to reply and gave us all the information we needed on the local area and beyond, even organising a taxi to take us to a local vineyard. The villa is beautiful and well-stocked with everything we needed. Genka had even thought to provide plenty of mosquito repellent for the house! Everything was clean and in good order and someone came each day to clean the pool (which we used a lot!). There are a couple of small shops and a supermarket close-by. The villa is situated on top of a hill, from which you can watch the sunrise in the morning and the sunset on the other side of the house in the evening. We will find it very hard not to book Genka's villa every year for our holiday! Grazie mille, Genka!

Lilium,delux farmhouse in the chianti hills
We had a fantastic stay at Concetta's beautiful home! The house itself is gorgeous and traditionally Tuscan. It is also in the most incredible scenery and sitting outside and taking in the view was an absolute joy. However, by far the best thing about our stay was Concetta and her husband Paolo. They could not have done more to make us feel more at home and it honestly felt like we were part of the family while we were there (including making us the most incredible meal, which I would strongly recommend you do if you stay!) Their hospitality, helpfulness and warmth made it feel like a true escape and I could not recommend it more.

The twigs
Sandrine’s Airbnb was by far the best accommodation we’ve ever experienced—a peaceful paradise nestled in the hills of Tuscany. What made it truly unforgettable, though, was the incredible generosity of our hosts. Sandrine welcomed us with a warm smile and thoughtfully provided delicious food and drink throughout our stay. She also shared wonderful recommendations for places to visit and things to see. It was a true blessing to meet such kindhearted and gracious people. 🙏

la Balza
We loved our time at La Balza - such a picturesque, peaceful and relaxing stay! Alessandro and his parents were a pleasure to deal with and answered all of my questions very quickly. They were very hospitable and accommodating. The area surrounding Radda in Chianti is absolutely beautiful and we loved the easy access to so many different cities and small villages. Would definitely recommend. A+

Villa Le Rocche with pool, breathtaking view
Incredible villa, meticulously maintained gardens and fruit trees, mesmerizing views and the gorgeous pool. Celebrated my father’s 70th birthday here with his kids and grandkids and we won’t forget it. Slice of heaven.

Casa Quinti, let yourself be surprised by beauty.
We highly recommend Casa Quinti. Beautiful villa, surrounded by authentic Tuscan nature. Irene did a great job at welcoming us and giving us recommendations. We went with our three little kids all below 5 years old and they loved it, especially the pool. The house had everything we needed. Grazie Mille!
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Lago di Isola Santa
- Medici Chapels
- Spiaggia Libera
- Cavallino Matto
- Teatro Verdi
- Palazzo Vecchio